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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
Vineyard View Retreat • Fire Pit • Wine Perks
2 bedrooms, 3 beds, 2 private bathrooms
16–21 Nov
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4.96 out of 5 average rating, 98 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.98 out of 5 average rating, 183 reviews
Top guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 124 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 272 reviews
Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 77 reviews
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
4.96 out of 5 average rating, 85 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
12–17 Sept
Guest favourite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 73 reviews
Guest favourite
Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 9 reviews
Luxe
Home in Healdsburg
3 BR | Saltwater Pool | Spa | Walk to Wineries
3 bedrooms, 6 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms, 3 king beds, 2 bathrooms
14–19 Nov
4.93 out of 5 average rating, 180 reviews
Guest favourite
Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.92 out of 5 average rating, 133 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 102 reviews
Top guest favourite
Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom, 1 queen bed, 1 bathroom
9–14 Nov
4.95 out of 5 average rating, 227 reviews
Superhost
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
4.9 out of 5 average rating, 266 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 53 reviews
Top guest favourite
Cottage in Healdsburg
Creekside Cottage
2 bedrooms, 3 beds, 2 bathrooms
29 Oct – 3 Nov
4.96 out of 5 average rating, 92 reviews
Top guest favourite
Guest house in Healdsburg
Designer Cottage | Garden Oasis | Walk to Plaza
1 bedroom, 1 queen bed, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 259 reviews